My Fake Fiancé
by jenniepennie
Summary: When Elena's invited to a frenemey's wedding, she can't show up dateless and pathetic—even though she is dateless and pathetic. So, Elena hires a hottie to pose as her perfect fiancé. But when he needs her to return the favor, Elena starts wishing the fake relationship was real. Can they turn their lies into love? AU AH
1. The Beginning

**Summary: ****When Elena's invited to a frenemey's wedding, she can't show up dateless and pathetic—even though she is dateless and pathetic. So, Elena hires a hottie to pose as her perfect fiancée. But when he needs her to return the favor, Elena starts wishing the fake relationship was real. Can they turn their lies into love? AU AH**

**Disclaimer: I own nothing. No copyright infringement intended.**

**I got this idea from a short story by Lisa Scott. I didn't read the story but was intrigued by just the summary so I am going from there. I know I still have two other stories, but at the moment they are both becoming kind of depressing for me, for personal reasons. But anyways I hope you all enjoy this one. Please review and let me know what you think!**

* * *

I grumble in annoyance as I walk towards my house. It was another ridiculous night at the Mystic Grill. Sometimes I hate where my life seemed to end up. Here I am 25 years old, single, and with a dead end job. How did I get here? I was in college for Christ sakes! My future was promising and bright. Oh yeah that's right I fell in love. Stupid stupid me! I grab the mail before walking into my house.

"Honey I'm home!" I yell out to no one in particular. Well not really no one as I see my bubbly bright friend Caroline walk around the corner from the kitchen.

"Hey, 'Lena, I got dinner in the oven… frozen pizza if that's okay." She smiled at me. The one thing about me and Caroline is that neither of us can cook to save our lives. We almost came close to burning down the house on our few attempts at a home cooked meal.

"It's fine, Care, I'm going to go take a quick shower and then I will be down." She nodded and went back into the kitchen. I walk upstairs to my room and run my fingers through my hair. My thoughts wander to my college days when I was so in love, and then everything changed when I found him sleeping with another woman. It was unbelievable. I was so devastated I dropped out of college and returned to Mystic Falls, where I am now the head bartender at the local pub… the only pub in town. I absentmindly fumble through the mail until my fingers hit a glossy envelope. I glance down at the envelope that had my name written in elegant script. I open it up and am stunned at what I see.

_Stefan Salvatore & Katherine Pierce_

_Invite you to share in their love and wedding vows on Saturday July 8__th__ at Central Park in the beautiful city of New York._

I walk slowly down the stairs, not bothering with my shower, and turn the corner to the kitchen. Caroline was chatting away happily on the phone until she saw me. I stare numbly into space, a million thoughts careening in my head. Caroline abruptly hung up the phone.

"Elena, what's wrong?" Not answering her, she glances down at the invitation that I was still clutching in my hand and rips it from my grasp.

With an audible gasp, she looks up at me her gray eyes full of sympathy, "Oh my god that asshole, how could he do this?"

Suddenly an idea formed in my head. Why should I let this bother me? I should go to this wedding and show them that what they did to me in the past doesn't bother me one bit. Yeah, I can do this. I try to convince myself that I can face the man who broke my heart by sleeping with that _bitch. _

"Care I'm going to the wedding." I blurt out.

"No. No. No!" she glared at me disapprovingly, "You are nuts if you think you're going to this. 'Lena you shouldn't torture yourself over this."

"Who says anything about torture? The wedding is next month and it gives me plenty of time to fulfill the plan I got in this wacky brain of mine." I wink at her and grab the pizza out of the oven as the timer went off.

"Plan? What plan, Elena?" Caroline stomped her foot at me. Typical Caroline, taking everything to the next level.

"I will tell you soon, I promise." I slice the pizza with my back turned to her. Can I do this? Even though Stefan slept with that slut, he claimed he still wanted to be my friend. We were only together six months and I obviously took the relationship more seriously than I should of. Maybe I need to do this so I can finally move on.

"Ugh, 'Lena, I hope this is something that's not going to backfire in your face." She grumbled through a slice of pizza.

Me too, I thought. Me too.

* * *

The next morning I woke up, I went outside to grab the newspaper. Since Caroline was at work at her clothing boutique, which I was quite proud of her since she could design the most amazing clothing ever, I grabbed the personnel section. I decided if I was going to put my plan into action I better get moving since I only got a month till the wedding. My eyes travel to the dating section and I laugh at some of the ads.

_Man seeking horny brunette to fulfill his needs._

Ugh, really? I giggle to myself that some men are so damn desperate. Alright on to the next one.

_Man seeking quirky blonde with ambition and who knows how to have fun._

I circle that one. Not for me of course but for Caroline. She's always complaining about being single. I look at the next one and my eyes widen.

_Need an escort? Need a date to an event and don't want to be the only single one there? Well you're in luck, write down this number and call today. For woman only who are seeking a male escort._

I hastily write down the number and grab my cell phone. I punch in the number and hit send before my overactive brain gives me second thoughts. I run my hand through my brown locks and bite my bottom lip in anticipation.

"Hello," a sultry voice answered.

"Hi, I – um, hi – yeah, I'm calling about the escort services," I say nervously. My nerves were starting to get the best of me, but damn did that man sound hot on the other line.

"Well what do you need sweetheart? Some sex? A date? Maybe just some sex?" The sultry voice chuckled.

"Trust me; I don't need to pay anyone for sex." I huff annoyingly into the phone.

"Well, then what do you need?" the voice drawled out.

"A date. I need a date to a wedding that's happening in a month in New York." I answer.

"Hmm, New York you say? I _guess _I can make room for you pretty thing. You are a pretty thing aren't you?" He chuckled softly to himself. I can almost imagine he was smirking. He seemed overly cocky, but I guess in his profession you would be.

"Wait a minute. _You_ would be my date?" I ask with trepidation. Not so sure I want to go with someone so damn arrogant.

"Of course, beautiful, you did call me you know." He answered back.

"Are you from Mystic Falls?" I ask.

"Of course I am, why?"

"Then meet me at the Grill." Before he can say anything I added, "If you're going to be my date to an important event, I need to see what you look like at least." I bite my lower lip anticipating his answer.

"Fine be there at noon."

"Wait how will I know what you-" he hung up before I could even finish. How will I know what he looks like? Have I ever seen him there before? This is going to be interesting.

* * *

Before I walk into the Mystic Grill I check myself in the review mirror. Smokey eyes check. Curly hair bouncing around my shoulders, check. I glance down at my outfit and smirk. No guy could resist me in this. I was wearing a red halter top with a V-neck that showed just the right ample amount of cleavage, skinny jeans, and five inch red heels, so sexy outfit… check. Why I was going overboard was beyond me, but I really need a date and someone that wasn't going to back out on me.

I walk into the bar and wave at Matt who was currently tending the bar. He waves back and smiles. I walk up to him and ask him to make me an apple martini, which was my favorite drink. While he was making my drink, I wonder why I just don't ask him. Why go through all the trouble of paying someone to pretend to be your boyfriend or fiancée. Haven't decided which yet. But I knew why, I look at Matt's blond locks, I like my guy's dark. Besides Matt was just a co-worker. Nothing more. We were barely even friends in high school. He places my drink in front of me. I glance at the clock behind him, 11:58… he should be here soon. Whoever he is.

I spin around on my stool and glance around the bar. I am pretty sure that the old horny bastard that keeps leering at me is not _him._ There was a cute guy with a navy style haircut, but he was preoccupied with the blonde in front of him. I spin around facing the bar again. Lost in my thoughts it barely registers that someone sat down next to me.

"Gimme a bourbon, Matt." A husky voice said.

"Sure no problem, man." Matt went to pour him his drink.

I glance up at the man next to be and am rendered speechless. White milky skin that seemed to contrast with his raven locks that fell over his forehead in waves. And my oh my. Those piercing blue eyes that were staring right into my brown ones. I blush slightly as his gaze roams over my body, and he seems to nod approvingly to himself. I should be annoyed and totally turned off but I wasn't. I was absolutely fucking hypnotized by this man's eyes.

"So I take it you're the one in need of a date." He stated and smirked my way.

No. Fucking. Way.

Shit, if he's the guy I'm going to pay to be my date I am so screwed but the only thing that came out of my mouth was, "I'm Elena." I hold out my hand for him to take. He takes my hand in his and shakes gently. Sparks flowed up my arms at his touch and for a second I wondered if he noticed too. He releases my hand.

"I'm Damon."

* * *

**Hmm what do you think is going to happen now? Let me know your thoughts! Big thanks to kayagirl99 for the beta! =) **


	2. Can I do this?

**AN: First of big thank you to kayagirl99 (Jessica) for beta-ing this story for me, you did awesome girl! Secondly, BIG THANK you for all the reviews so far! I was stunned and floored that the first chapter got 16 reviews! Plus 12 Faves and 37 Follows! Wowowow. How about we get thirty reviews this chapter? Just kidding. Maybe. ;) I hope I continue to do this story justice. Okay now read on and review please! :)**

* * *

My mind is still reeling over the sparks that flowed up my arm at our slight contact of skins. Damon sips on his bourbon while penetrating me with those damn blue eyes of his. Doubts start to form in my mind about what I am doing. This is absolutely crazy to say the least. I'm desperate, but am I _that _desperate? Don't get me wrong the man in front of me is a god. The way his muscles flex through that black t-shirt of his, would make any woman drool. But I would be paying him. To pretend he loves me. Do I want that? I look him over once more. My eyes travel from his hair to his eyes, chest and down. Yea no way in hell can I do this? Maybe I should just ask Matt, from what I have been told from both Bonnie and Caroline is that Matt has always had a secret crush on me. Wouldn't it be better to do this what someone who at least likes me? With my mind made up I spin around, giving Damon the once over once more.

"I can't do this, I'm sorry." I place money on the bar for my tab and stand up to walk out.

Damon surprised me by grabbing my arm lightly, causing me to look at him once again. "How about I give you half price then?" He whispered softly so that no one can hear.

"Damon, it's not about the money." I muttered softly, grabbing my purse.

"Then what is it about?" He asked, curiously.

Damn, this man was persistent. By the looks of him it's not about the money at all. Something was swimming in those heavenly blue orbs of his that I couldn't quite decipher.

I sit back down on the bar stool and cradle my head in my hands. "It's complicated." My eyes pleaded with his to not ask any more questions. But apparently he didn't get the drift and continued anyways.

"Life is complicated. Life is cruel and unkind to people. But this," he said pointing in between the two of us, "Should be easy. Yeah we don't know each other, but I know you felt what I felt earlier. So yeah I think we should do this. You look like you need it. Though I don't understand how a beautiful woman like you would be desperate for a date, but I can use this, too."

I blush slightly at his words. So he felt it too? And he thinks I'm beautiful? I giggled slightly to myself. I know I am not unattractive, but it just amazes me that someone like him, who obviously has money and is so damn good looking, would be interested in helping me.

"Fine." I reluctantly give in. He nods at me and smirks.

"So whose wedding are we going too?" he asked curiously.

I tell him who it is. Giving him the whole story how me and Stefan once dated. I figure since this would just be a one-time affair why hide anything from him. Most likely after next month I will never see him again. When I mentioned Katherine, a fire that I haven't seen yet, passed through his eyes. Wonder what was up with that. Then I told him how me and Stefan broke up, yet he wanted to remain friends. So I guess that's why he sent me an invitation. I told Damon how I was the one that was probably more caught up in our love affair than he was. And it could be true. Scratch that probably was true, since me and Stefan were good friends before we decided to make it intimate.

Taking a sip of my new drink that Matt made me, I wait for Damon's reaction. He was currently looking at his glass of bourbon with narrowed eyes.

He looked at me then and gave me a lopsided smile, a smile that I was finding to be quickly endearing.

"Well, I guess his loss is my gain."

"Maybe so, but I decided to go along with it and show him how I moved on. I need to do this, not for him, but for me." I needed to be able to prove to myself, that I am not pathetic, and that I can find a great guy. Yeah, even if I had to pay someone.

"Hmm… how about you and I make a little deal?" His velvety voice dangerously low. Damnit, why is his voice making things in me tingle that never did before?

I can feel his eyes on me waiting for me to say something.

Out of curiosity I ask, "What kind of deal?" I am a little uncertain about this; I have a bad feeling things are going to end badly if we make _any _kind of deal.

"Well, you need a date in July, correct?" His eyes are still on me searching my face. What he was searching for I have no clue. I nod 'yes' to him.

"I was thinking you might be able to help me with my problem. You see, I have a wedding also coming up in August, and I need a date. If I don't have one I will be pushed into blind date after blind date that I don't want to have for my own reasons." He sighed wearily to himself, seeming unsure about what he was trying to say. "So what I am proposing is this… you don't have to pay me any money if you agree to do this favor for me." He finished his heavy eyes still on my features.

"So, what you're saying is, if I agree to be your date, I don't have to pay you. If I don't agree I have to pay you." I stated clearly to him.

"Yep." He said popping the 'p'.

I weigh the pros and cons of this situation in my mind. My heart keeps screaming, yes go for it! While my mind is saying no and that in the end I will just end up hurt. Should this be a risk I was willing to take? I studied him curiously. He seemed like a decent guy. Although he was cocky, he had that sexy smirk that keeps making my insides feel like jello. There was something in the depths of his eyes that he was hiding though. And I was damn curious to find out what it was. So with my mind made up I give him my answer.

"Okay, I will do it. On one condition, though." I take a sip of my drink my eyes never leaving his.

"And what is that, Miss Elena?" He asked slowly.

"We do this; there will be absolutely no sleeping together. As in two bodies tangled up, naked sleeping together." I stated firmly. I know if we sleep together, it will just cause problems that neither of us need. We need to just do these favors for each other, have a little fun, but just not _sexual_ fun. His answer surprises me and I found it kind of hurtful.

"That won't be a problem."

* * *

**This chapter is broken down into two parts since the meeting between Damon and Elena is not over yet. There will be plenty more of these two next chapter. Plus it will be even longer! :)**

**Oh and as a note I previously mentioned in the first chapter that Damon and Stefan are not related. Well I changed my mind they ARE going to be related. It will just make the story that much more interesting in my opinion. Well hope you all enjoyed this chapter! Please review! **


	3. Madness

**Wow I am absolutely blown away by all the reviews so far! Thank you so much to everyone who has been reviewing, it makes my day and keeps me going to continue to write this story. I got a nice long chapter for you all, over 3500 words! Since I am ahead a couple chapters figured I give you all an early treat. Please READ AND REVIEW! Let me know what you think even if its to say you hate it :)**

**And again big thank you to my beta Jessica (kayagirl99) for looking over this chapter for me! :)**

* * *

"_When love is not madness it is not love."_

_―__Pedro Calderón de la Barca_

…_._

I mock feign hurt and pout at him, "I can't believe you don't want to sleep with me."

He laughed a sound that was rich and musical to my ears. "Were you not just the one to say and I quote there will be "no sleeping together"?" He put his hands up in the air and made invisible quotation marks, a smile still plastered onto his face.

"Yup." I said popping the 'p' like he did earlier.

He muttered to himself and shakes his head and glared at me. "Women."

I stand up and place my hands on my hips, tapping me toes on the tiled floor. "Well this 'woman' will be helping you, so you better be nice to me."

He smirks at me and gazes amusingly at my current stance.

"Trust me I can be a whole lot of nice." He leaned over and whispered in my ear. My breath hitched in my throat at the feel of his warm breath sending tingles down my spine. "And I can be a whole lot of other things as well. I can show you things you never seen before." He added seductively before pulling away. His smirk was still on his face.

"Trust me I am sure I have seen it, and done it, so nothing new there." I retort back.

He claps his hands together and continues to smirk. "Anyways on to business." His playfulness suddenly gone. How he can go from flirting to businesslike in a matter of seconds was beyond me.

"We need to decide how we are going to do this. I have my ideas, but you need to be willing to make them work." He said in a firm like business tone.

"What do you propose?" I will admit I am weary about his ideas, but he has a right to them.

"I think we should pretend that we are engaged. That when you moved back to Mystic Falls, we met and fell in love. I didn't tell my side of the family yet, and you didn't tell yours because we wanted to make sure it worked before we became public about our relationship. To hold up the charade on my side, we need to start pretending, like right now that we are engaged. Your whole ordeal will be a piece of cake compared to mine, trust me on that. So you need to be prepared with what your facing." He finished his proposition.

He took one good long look at me before turning his attention back to his now empty glass of bourbon. He lifts his empty glass at Matt singling for another one.

After Matt pours him his drink I bring my attention back to the man before me. Two months of pretending to love this man was crazy. It seemed to be way more than I bargained for. But it could be fun, right? Matt came over with my third martini and joked how I was officially cut off. I smirked at him, and placed my hand on Damon's knee and leaned over giving him a soft peck on his stubble cheek.

He looked at me surprised. But the effects of my third apple martini were making me feel bold at the moment. "What?" I innocently ask. When I didn't get an answer I added. "If we are going to do this, we need to pretend, right? So why not start now." I giggle at his stunned expression. He looks me over his features turning back into that adorable smirk of his.

"You are right, but you need to move your hand." He warned, but winked when I looked down. I snatched my hand away quickly not realizing in my mindless rubbing of his leg how dangerously close I was to a now evident bulge in his tight black jeans.

I blushed furiously and took a big gulp of my drink. At least I know I have the same effect on his libido as he does on mine. How I can go without touching him and it not doing something to me was going to be hell to say the least.

"There is someone that needs to know the truth though." I said in hopes to get off the subject and distract my brain that seemed to lose all train of thought.

"But we just –"Damon started but I cut him off.

"There is my roommate Caroline that needs to know. She is already suspicious of me because of my reaction yesterday to the news of being invited to the wedding. She knows me Damon. Besides her and Bonnie, who is currently in New York, but we can deal with her later." I know I have a logical explanation but Damon seems uncertain about it.

"Fine we can do it." He reluctantly gave in. "But she is the only other one that can know about this arrangement." He added.

My thoughts start to wander to our current arrangement. A soft smile spreads across my lips. I begin fantasizing what life would be like if Damon and I met under different circumstances. I imagine that his smirks and laughs would still be there, but there be more physical contact. Physical contact that for some reason my skin seems to be screaming for. The jolt of electricity that I would feel pass through us every time we touched, even for the briefest of moments was exhilarating.

"Hello, earth to Elena." Damon waved a hand across my face distracting me from my thoughts.

"Hmm." I mutter still lost in thoughts.

Damon smirked and stood up putting on his leather jacket. "I _said _I got an appointment so I need to go." He placed two twenty dollar bills on the counter and said it was for mine and his tab, and he placed a piece of paper in front of me. I stared at the address written on it confused. When Matt walked away Damon turned to me again and whispered in my ear. "That's my address, I would like for you to stop by tonight." And with that he walked away and out the door.

The heat of his breath was still on my neck and my heart hammered away in my chest. I look at the clock and notice it's was now two. Since I wasn't working tonight and didn't want to be here anymore, I grabbed my purse and waved bye to Matt before heading home.

* * *

I didn't even notice when Caroline sauntered into my bedroom. I was lost in thought while gazing at the picture of my parent's on my mirror. How I wish my mom was here to help me in my current crisis.

"Elena, did a tornado come that I didn't know about?" Caroline stood at my door with wide eyes while taking in the current situation in my room. I look around at the disarray of outfits scattered on the floor and my bed. I sighed with annoyance and plopped down on my bed sending some articles of clothing on the floor.

"I don't know what to wear!" I yell out pulling at the ends of my hair.

"Does Elena Gilbert have a hot date that I don't know about?" She exclaimed excitedly, while walking over to my closet and sorting through my clothes.

"Not exactly."

"Then why all this unnecessary drama?" She eyed me suspiciously.

I started to tell her about my day's events and about Damon. Her grey blue eyes were wide with surprise and after picking out a pair of five inch heels, a black mini skirt, and a silky blue top; she spun on her heels and glared at me.

"I can't believe you're doing this!" She said with obvious annoyance in her voice while flinging her arms in the air. "And who the hell is Damon? Does he live here because I never heard of him before."

"I don't know Care. He seems kind of low key, and yes he does live in the area apparently." I didn't know what else to tell her because I don't even know that much. Yet.

"Well if you are both just doing each other favors like you said, then why all the drama on what to wear?" She wagged a finger at me.

"Not sure." I mumble. I don't usually go so overboard unless it's a guy I am actually dating. Well we are sort of dating, aren't we?

"Humph." She threw the outfit she picked up at me and was starting to walk out the door.

"Wear that."

"Wait a minute what do you mean "Humph"?" I noticed her change in behavior and it had me curious. Almost like she held a secret I didn't know yet.

"Nothing 'Lena, just wear that outfit. I am sure things will work out like you want." With that she walked out the door too her bedroom.

What the hell.

* * *

Still confused with Caroline's behavior I pull into Damon's driveway and gawk at the boarding house in my line of vision. I've seen this place before but always assumed no one lived here. It was massive and for one person only? I am pretty certain Damon must be the only one living here. The only other vehicle here is a blue Camaro, which I can only assume is Damon's.

I park my car and walk out hesitantly. I glance down at my outfit that Caroline picked. Now it seemed like a bad choice because I am not here for a date. Just to talk about our arrangement is all. Should have just gone with my standard jeans and heels. Not a damn miniskirt and a tight blue silky shirt that hugged my skin. I walk to the door and knock softly and then loudly since from the looks of it is a big house, lord knows where he is inside of it.

Damon swung open the door with an apron on that read 'Kiss the Cook.' His eyes traveled from my hair that I straightened to my hips where they were currently paused. I shifted on my feet uncomfortably. His eyes snapped up to meet mine.

"Come on in." He stood aside so I could enter. He closed the door behind him.

"I prefer your hair straight." He blurted out, a hint of a blush on his cheeks.

My mouth opened to say something and then closed and opened again. I wasn't expecting a compliment like that so all I could muster was a simple thank you. It was then that delicious aromas invaded my nostrils and I gaze at him curiously.

"You cook?" My mouth fell open again at his simple nod of his head. Damn this man can do anything! From going on dates and getting paid to living in a mansion and being able to cook. I was amazed and started to wonder about what other abilities he had. And those thoughts only seemed to pertain to the bedroom area.

Snapping me out of my thoughts he simply said, "Well dinner is almost ready."

Even though I ate a little sandwich before I came here because I wasn't expecting a dinner, my stomach growled loudly. I blush slightly and followed him as he headed towards the kitchen. He had a dining room table all set up with two glasses of wine and a candle in the middle. I was confused at the romantic display but just rubbed it off as being part of the act. We would have to be used to acting like a couple eventually in front of people, might as well practice in private.

He then places a plate in front of me and goes and sits at the other end of the table. He looks at me with a glint of mischievousness in his eyes. I look down at my plant and gasp at the delicious look of pasta and chicken parmagiana in front of me. It was so mouthwatering and when I dug in and took my first bite and exhaled a loud moan, I blushed as I noticed Damon was staring at me.

"This is absolutely delicious!" I tell him in all honestly. He smiles softly and mutters a quick thank you. That damn lopsided smile was going to be the death of me. I found myself wanting to make him smile like that all the time.

"Do you live here by yourself?" I ask curiously.

"No I live here with my best friend Alaric and his fiancée Jenna. They are currently in New York shopping for the wedding and spending the weekend there." He said in between bites of food. So they must be the ones he wants me as a date for.

"Jenna, as in Jenna Sommers?" I knew a Jenna, but it couldn't be the same one.

"Yes, why do you know her?"

I drop my fork and knife and smiled brightly. I couldn't believe he knew Jenna! I heard from word of the mouth she was getting married, but I never had much opportunity to talk to her. Now that I think about it I am not even sure she knows I am back. Yeah I work at the Mystic Grill but from what I remember she was never a fan of the place. She had bad memories of a former boyfriend, whom she use to frequent the Grill with. I only been back 6 months, which was another reason I was so shocked Stefan was getting married. Made me wonder how long this thing was going on between Katherine. I suddenly realized I was so lost in my thoughts that I didn't answer Damon.

"Jenna and my mom were great friends. Before I went off to college Jenna lived with me." I tell Damon. I remember how I used to tease Jenna and call her Aunty. Even though she wasn't blood related she was always what I envisioned an aunt to be like. When I went to college she rented the house to Caroline who stayed here to open her shop. Now that I think about it, was I so lost in my own world where I failed to not notice other people? I felt like a horrible person and had the urge to apologize to Jenna.

"She never mentioned that." Damon said surprised.

"She wouldn't. She loved my mom, and it hurt too much to talk about."

"Well this is going to be interesting when she hears _you're_ my fiancée." Damon said with a smirk on his face. He started clearing off the table, and refilled my glass of red wine that I didn't even notice I finished. I took a sip enjoying the warmth that spread through me.

"Yes it will be." I smile at Damon knowingly. Jenna is going to flip and wonder why no one told her a damn thing. I cringe at that thought as my guilt came to surface again with not talking to the woman that took care of me through a hard time.

"Speaking of, why did you ask me here?" I pointed out the reminder that I knew there was a reason why I was here just wasn't sure what it was yet.

He walked over to me and took my glass of wine and led me into what was the living room. A fire was going in the fireplace and we sat on the couch in front of the fire. I took another sip of wine and placed it on the table awaiting his answer.

He reached in his pocket his eyes never leaving my face and held out an object to me. It was a ring. A beautiful antique looking diamond sapphire ring. It was in the shape of halo with smaller diamonds wrapping around the blue. It was absolutely stunning, but why was he showing this to me?

"I figured if we are going to do this, we need to do it the right way," He began softly. My heart pounded in my ears and I started to feel a little dizzy. I know this is pretend but he doesn't need to propose! "This was my mother's ring, and I am trusting you with it for the next two months. I want you to wear it because this is what I would have given the woman I love." He takes ahold of my left hand and slipped it on my wedding finger. I marveled at how it seemed to fit so perfectly. Like it belonged there.

"Perfect fit." He mused.

Thinking I found my voice, a breathy whisper came out instead, "Damon I can't wear this!" I went to take it off to hand it back to him but he stopped my actions laying a hand over mind. The touch sent sparks through my body.

He kept his hand enclosed on mine, "Yes you can, it will be just more believable this way." He insisted.

He releases my hand and walks over to a mini bar near the fireplace and pours himself a glass of amber liquid that I could only assume was bourbon. "This is not the only reason I had you come here." He sat back down beside me sipping his drink. "We need to come up with a cover story."

"Since we need to see if we can pull this off next week, we better come up with a story." He said simply.

"Next week?" I was confused why so soon. I know this was a two month arrangement, but still.

"Yes Alaric and Jenna will be back and I am not waiting to introduce you as my fiancée till their wedding." He reminded me.

"Right, well since my emotional health depends on this we better do it right." I reply sarcastically, but smiled so he knows I am joking.

"Hmm well we need to figure out how we met. What I do that drives you crazy – in and out of bed – and the sweet sickeningly way I proposed to you." He winked at me as his lips curled up into his famous smirk.

"Well one thing that drives me crazy right now is how it seems like everything you say has some sort of sexual innuendo." I pointed out annoyed at myself that words out of his mouth feel like fingers caressing my skin.

"Do I now." It wasn't even a question and I decided to change the subject. There was only so much of his dangerous flirting my heart can take.

"So did we meet through work?" I ask, taking another sip of wine delighting in the way it made my senses tingle. Or that could just be the near proximity of Damon.

He frowned at that. I guess he would because of his profession. "How about we just say that we met at the Grill? And my profession won't matter on your side since I also own part of a business in New York."

"Okay that's fine." Surprised at this new information. I wondered what kind of business it was.

"Why do you love me?" he asked that mischievous glint back in his eyes.

I blinked at him. Anyone could take one look at him and see why I love him. Well theoretically speaking that is.

I tried to list the reasons in my head to form into words. "Because you are successful, driven and wild in bed."

He wagged a finger at me. "No, no you're the wild one. I can hardly keep up. All the places you wanted to have sex drained me dry." He smiled deliciously at me.

I blushed slightly because in that moment I was imagining all the places we could have sex right now. I rubbed my thighs together to ease an ache that was quickly forming.

"Okay that's for my part. I guess you can figure yours out as we go along with this charade."

"Charade?" He asked with mock hurt. "But I thought you loved me."

I laughed and slapped him lightly on his chest. "I am getting a little too buzzed right now. Might have to finish this conversation another time." I finished my glass of wine, placing back down on the table.

He finished his bourbon and places it next to my wine glass and scoots closer to me. "There is one more thing I want to try before we end this for the night." He whispered his face a mere few inches from mine.

I swallowed thickly at the lump that formed in my throat. "And what is that?"

The corner of his mouth twitched up slightly and his heavenly blue orbs latched onto my brown ones. He leaned closer to me his hands coming up to cup my cheeks. My heart pounded violently in to my chest. If I leaned forward just a little bit my lips would touch his, but I didn't. He sighed softly his warm breath caressing my lips before he latched his lips onto mine. Our lips seemed to mold together perfectly and even though my brain was yelling stop my hands had a mind of their own when they crept up into his raven locks. I parted my mouth granting him access and the kiss became more aggressive. Electricity coursed through me, as my core throbbed with ache and need. It's been so long since I had someone touch me like this. Let alone kissed somebody.

I pushed him away slightly not pushing him too far. We gazed at each other in wonder, both of us breathless.

Holy Shit. That was HOT.

Before I knew it I pulled him to me again, getting lost in the moment that was just Elena and Damon.

* * *

**Don't get too excited ;) I'm not really going to make it that easy for these two :D Please read and review!**


	4. We All Become What We Pretend to Be

**Wow! Thank you so much for all the great reviews last chapter! I can't believe at only 3 chapters I am almost at 50 reviews! I wasn't expecting this story to grab the attention of so many people! Just a note this will probably be the last chapter for this week. Next chapter probably won't be up till Sunday or Monday the latest. I am just really busy this week, but will try my hardest to get one up fast! **

**Big thank you to Kayagirl99 (Jessica) my fabulous beta you rock! **

**Read and Review!**

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"_We understand how dangerous a mask can be. We all become what we pretend to be."__  
__―__Patrick Rothfuss__,__The Name of the Wind_

When I all of a sudden found myself straddling Damon, I jumped up and began pacing the floor back and forth. Running my fingers through my hair I try to say the words I want to say but nothing comes. Damon looks at me with a confused expression on his face. He looked absolutely ravishing. Still wearing his "Kiss the Cook" apron that he failed to take off and his hair messy and red swollen lips, I wanted to jump back in his lap. But I couldn't. This was not supposed to be happening!

"We can't do this." I state, tugging at the ends of my hair.

He looks up at me and nods in understanding. He sat up and flashed me a wide smile. "Well at least now we know that no one can deny there isn't an attraction between us." His smile changed into a smirk, which was beginning to irritate me.

"Right, of course. I think the best solution is that we shouldn't be alone. Like ever." I insisted. Seemed like the only logical solution at this point. Though I would love to know what can happen, I will just live with my fantasies instead.

"If you insist." He grinned at me.

"Yea, I do. I got to go, Damon. I will see you later." I grab my purse and straighten out my skirt, which I failed to notice was riding up my thighs. My heart was still slightly pounding but not as bad as before. I debated about leaning over and giving him a peck on the cheek but decided against it. That will just be reserved for fake public affection. Not private.

As I was walking out towards the door, a hand grabbed my elbow spinning me around. I look at Damon confused and the close proximity of our bodies again was turning my brains into mush.

He looked at me with furrowed brows. "I am sorry if I pushed you to do something you didn't want to do, I didn't mean too." His eyes spoke his sincerity, and I was confused as to why he was apologizing. Was I the one not straddling him just a few minutes ago?

"It's fine, Damon. I just don't want us to lose sight of this mission we got planned by getting wrapped up in whatever this is." I smile softly. He still looked uncertain, so I leaned on my toes and kissed his cheek softly. I pulled away and thought I saw a hint of vulnerability but it was gone and his famous smirk plastered on his face.

"Ah, so you do admit there is something." He smirks, smugly

"Damon, good night." I shook my head and turned around smiling to myself and walked to my car to head home.

* * *

The next morning I was sitting at my kitchen counter sipping on a much needed cup of coffee. I didn't get much sleep the night before, due to my overactive brain that kept picturing a naked Damon pressed against me. How I am going to survive these next two months is a constant thought in my mind. Maybe I should wear a chastity belt and throw the key away. I chuckle to myself at that thought. Thank god for porn stores and my trusty vibrator that I keep in my nightstand. Without that I am screwed.

"Boy someone looks happy this morning." Caroline said sarcastically, wiggling her perfect brows my way.

"More like sexually frustrated." I mumble taking another sip of my coffee.

Caroline laughed her blond curls bouncing on her shoulders. I glare at her because she always teases me about not getting laid.

"Isn't the whole point of you and this Damon is so you can indulge in each other?" She smirked and lifted curious brows my way.

"It's not like that Care." I groan, frustrated. The whole point is to get through these next two months without sleeping together. I can't and won't deal with the emotional attachments that come along with sleeping with someone.

"Yeah sure whatever you say Elena." Her eyes wide as she looks at me, "You will be sleeping with him before you know it." She looked at me pointedly before adding, "Your sexual frustration is going to end up taking over."

I scoff at that. How she thinks I won't be able to do this is beyond me. I glare at her defiantly, "Well I will just be proving you wrong then." I empty out my cup of coffee in the sink and slam it down with a loud thud.

Caroline chuckles loudly at my retreating figure as I head back up to my room.

"You are going to regret this Elena! Mark my words just do it and get it over with! The sooner you have him out of your system the better." She yelled after me.

I slam my bedroom door shut and heard Caroline laugh once more. I leaned against my door annoyed and was almost tempted to kick Caroline out of the house. But I won't do that she is my best friend after all who has been there for me through thick and thin. Sometimes though she just knows me better than I knew myself. I was tempted to give in and listen to her, but my brain kept yelling at me to not too. So I decided to listen to my brain.

* * *

That evening at work was the most boring night of my life. The only nights I dreaded working were Sundays since nothing in particular ever happened. It was the usual crowd. Rarely were there ever new faces in Mystic Falls. I tap my fingers on the bar top and glance at the clock. Only one more hour left. One more agonizing painfully slow hour left. My phone vibrated in my pocket indicating a text message. I take it out and unlock my phone and noticed it was from Damon.

**Hey cutie be at my house tomorrow at 7 for dinner oh and wear something hot – D**

I smirked at that and can almost imagine his smirk as well. I haven't seen him since the other night in attempts to avoid being alone with him as much as I can. I was about to tell him to forget it, but then remembered tomorrow is Monday, meaning Jenna must be home with her fiancée Alaric. My heart flutters in my chest from anxiety. Since this will be the first test to see if we can pull this off, my nerves started to get the best of me.

**Sure not a problem… see you tomorrow wearing a brown paper bag – E**

I hit send and place my phone on the counter top. Within minutes my phone vibrates again. I glance around the bar making sure no patrons are in need of a refill and look at the message.

**You consider that hot? =/ - D**

**You really think I would do something like that? – E**

**I don't know would you? – D**

**Maybe ;) – E**

I laugh at the silliness of where these text messages are going. I never considered Damon as a gullible type.

**Hmm how about wearing nothing? ;) – D**

**Alright ending this conversation now lol see you tomorrow – E**

Of course in typical Damon fashion that I am beginning to get use to, he would turn it around to be sexual. The last thing I am going to do is start sexting or sexing him in anyway. My phone buzzed again.

**No! This was just starting to get interesting – D**

**Goodnight perve – E**

**You know u wanna get pervey with me ;) – D**

**Okay that's it turning my phone off now I got to close the bar bye – E**

With that I shut off my phone annoyed at the turn of the conversation. Now the only things going through my mind is me and a naked Damon. I can't let this get out of hand. I glance at the clock again. Ugh a half hour left. Maybe I should have kept texting him to stay busy. But this dangerous flirting is not good. Is that even what that just was? Flirting? Before I knew it the kiss from the previous night invaded my thoughts. No matter how far I tried to push it away it kept resurfacing.

A voice cleared their throat and I found myself drowning into an ocean. Lost in my thoughts like usual I failed to notice that someone sat right in front of me. That someone being none other than Damon.

"Damon." My voice squeaked.

He wiggles his eyebrows at me and gives me a half smile, "Elena. Since you shut your phone off and I had nothing to do thought we'd finish that conversation."

I blush furiously and regain control of myself and raise a perfectly arched brow his way, "Damon, we will be closing soon," I go and pour him a glass of bourbon, "drink this and be on your merry way, I will see you tomorrow." I slide his drink to him.

He pouts at me and I found it slightly adorable but kept my face composed. "You're no fun."

I slam my hands down in front of him causing his drink to rattle and ice cubes clink. I glare at him. "That's enough; this is supposed to be fun when we are around other people, not _alone _why don't you seem to get that?"

He finishes his drink in one long gulp and bangs it on the counter causing me to jump. I shiver at the coldness emanating from his eyes in my direction. "I will see you tomorrow then." He forced out and walked out of the bar.

I sigh heavily and start wiping down the bar top and putting the glasses in the dishwasher. I yell last call to the remaining patrons. Since there were only two they paid their tabs and walked out. I close the register and grab my purse making sure everything was shut off and lock the doors to the Grill.

"You know your mood swings are kind of giving me whiplash." A voice whispered in my ear as I was locking the doors. I jumped and shrieked and turn around to find blue eyes gazing at me, amusingly.

"Seriously, Damon, I am tired." I begin walking away towards my car. But, of course he decides to follow me and keeps up with my pace.

"You," he said turning around and walking backwards so that he was facing me, "need to learn how to have fun."

I glare at him and pinch the bridge of my nose, "I know how to have fun, Damon. That's what this is… fun." I go to open my car door but he traps me. I cross my arms over my chest anxiety coursing through me. We haven't even tried pulling this whole deal off yet and already we kissed, and fought, what the hell is next?

He puts his arms up on both sides of me trapping me in. "You want to know what I think? We won't pull this off if you keep letting your fear through." He whispers in my ear.

I begin shaking. Not from fear, but from the feeling of his lips brushing against my ear. "I am not scared." I tried to say evenly, but my voice faltered. His blue eyes swimming with amusement latch onto mine.

"Stop denying it, Elena. You are scared because you know you want me but you're scared to give in because this is just supposed to be a 'ruse'." He said with fire in his eyes.

Honestly, what scared me in this moment was how he seemed to know me so well. He knows he got under my skin, and he's using that to his advantage. Well, one thing was for sure; no way in hell was I giving in to him. We are both going to do what we planned to do and that's it.

I regain my composure and push him away from me, opening my car door. "One thing you need to get through your thick skull is that I _don't want you_." I said coldly hoping he gets the hint. I sit in my car and start it, rolling down the window to get some fresh air. I glance at Damon one more time who was running his fingers through his hair. Before I turn the corner onto the main road I hear him yell out.

"I think the other night spoke for itself, Elena!"

And how right he was.

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**Elena's mood swings are starting to give me whiplash, haha. Please Review and let me know what you think!**


	5. Now the fun begins

**Blah I am so sorry for the lack of updates. This chapter is actually not beta-ed since I wanted to get it out. I still hope you all enjoy it! And thanks so much to everyone who reviewed last chapter! I was blown away by the response. 23 reviews last chapter! **** I hope this one is good; I kind of lost my muse because everything in life right now is really sucky. From my own fiancé being in jail, to the place I worked at foreclosing so now I am out of a job, I just been really depressed. So yeah… **

**Anywho please read and enjoy and let me know what you think. Even if it is to tell me how it's the worst chapter ever!**

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_Now the fun begins…_

The next afternoon, I was tempted countless times to call Damon and tell him that I give up and would rather go to the wedding single. After a long talk with Caroline she convinced me to keep up the ruse and have fun. But I still had my doubts which inevitably almost had me not listening to Caroline's advice. Damon texted me a few minutes ago and said there was a change of plans. We were now going to a fancy restaurant out of town. That made me more nervous than it just being four people at Damon's house. Now we had to be around triple the amount of people! I know I shouldn't be getting so worked up, since when it comes to the weddings, there will be hundreds of people, but still. And Damon is also picking me up. So guess this was a date. Or was it?

The thing that I hated the most was the longer this goes on, will it be difficult to differentiate between the two? On what's real and what's not? My mind wandered off to my conversation with Caroline earlier this morning.

_5 hours earlier_

"_Really 'Lena you just need to chill." Caroline huffed at me when I told her what happened with Damon last night._

_I glared at her, wondering why she just won't agree with me._

_She sat down next to me on the couch and looked at me with her wide blue eyes. "You are reading too much into this arrangement you and Damon have. A little fun wouldn't hurt. And hell if you get laid you gets laid!" _

"_What? Care, but you know I am not that type." I said pointedly._

"_Yes I know that 'Lena, but it won't make you a bad person if you do it. You have fun with him for two months and that's all. Hell I do it. Got nothing to lose."_

"_Besides my dignity?" I throw my hands up in the air and continue to glare at her annoyingly._

_Caroline looked around the room obviously avoiding my gaze. "Okay I give up. 'Lena you always been the relationship type. I get it, I do. But you seriously need to let loose. You don't have to let Damon in, but you can have fun without it being __**too **__serious. No harm no foul. The only problem I see in this is if you want him to be more. You just need to decide for yourself." She stood up after her impassioned speech, leaving me sitting on the couch alone and even more confused._

Could she have been right? No doubt I picture myself sleeping with Damon, on countless occasions since I met him I envisioned what it would be like. But wanting more? No I don't because I see the type of person he is and he is not one to settle. He is a womanizer. Probably why he loves his job so much. I have nothing against his choice of work. Hell we all need to make money. But my curiosity was still peaked as to why he does what he does. Nothing wrong with getting to know him as a friend, right?

* * *

Couple hours later I stand in front of my mirror to admire my attire. I was wearing a simple strapless black summer dress that fell a little below my knees. It contrasted well with my olive skin, and hugged my curves in all the right places. I added a sparkling silver belt at the waste to give it some flare. For my shoes I was wearing my silver flat sandals because I thought with heels it looked like too much. I wanted my outfit to be simple yet appropriate.

Every time I looked at the clock I would bite my lower lip nervously. Damon should be here soon. I recheck my makeup and fluff my hair. I decided to leave my hair straight and my makeup natural. Didn't want to look like I was trying too hard.

The doorbell rang and I run down the stairs and almost tripped on the last step, I regain my composure and open the front the door breathlessly. There stood Damon in all his handsome glory. For once he wasn't wearing a black shirt. Wearing a crisp white button down shirt made his eyes seem even bluer, if that was possible. His raven locks fell neatly on his head and his black slacks and black dress shoes… he simply looked like a god. I was starting to think it was a crime that there should be anyone this beautiful walking the planet.

I blush, not realizing I was openly gaping at him.

He smirked amusingly at me, his eyes slowly traveling from my face to admire my outfit.

"Hello Elena." He drawled out. He always puts emphasis on my name and it was irritating me.

"Damon."

He walked up behind me before I could say anything else, and brushed my hair aside so that it was resting on my right shoulder leaving my left one bare. I shivered slightly when his fingers grazed my neck. I felt something cool around my neck and my fingers come up to touch the foreign object. I glance down and gasp and spun around to look at Damon. It was a beautiful pear shaped sapphire pendant that was surrounded my smaller intricate diamonds. It was on a simple yet delicate silver chain.

I was at a loss for words.

"This necklace was my mother's as well. Thought it would go good with the ring." He shrugged and smiled softly at me.

I glance down at my left hand and see the engagement ring. I was mesmerized by the blue of the sapphires. So much like his eyes. I didn't plan on always wearing this ring. Only when it was needed. It finally hit me in that moment that since he placed this ring on my finger I never taken it off.

Damon cleared his throat, and was standing back at the door. "So you ready to go Miss Gilbert?"

"Yes… and Damon, thank you, it's beautiful."

He looked momentarily surprised. I shut the door behind us and we head off to the restaurant.

* * *

As we pull up to the restaurant I nervously begin playing with the hem of my dress. Damon reaches over and entwines his fingers with mine. I look at our hands and then look up at him.

"It's going to be okay 'Lena, nothing to be nervous about." He smiles softly at me. I stare into his blue eyes and suddenly begin to feel myself relax a little bit. He points to a couple sitting on a bench outside the little quaint Italian restaurant. I immediately recognize the blond woman, whose head was bobbing up and down with laughter. She is with a sandy blonde hair man. He was very good looking in a boyish sort of way. I look at Damon and nod my head indicating that I am ready to go.

We get out of the car and walk towards the other couple. Damon again places his hand in mine and before I knew it he spun me around to plant a soft kiss on my lips. I wanted to pull away, but didn't. Well rather I couldn't. His lips leave mine rather too soon, and I gaze into his blue orbs and blush slightly. We took a few more steps and reached the other couple.

"Jenna and Ric," Damon smiles widely at the couple, who seem lost in their own little world. Wait a minute… I thought he kissed me because they looked at us? Before I could dwell on it anymore I heard Jenna gasp.

"Elena Gilbert?" She smiles up at me her eyes wide with surprise.

I blush slightly. "Hi Jenna."

She grabs me into a hug and I found myself welcoming her with open arms. How I missed her. Even though she wasn't blood related to me she was family.

She pulls away and holds me at arm's length, "Ric this is Elena, you know the girl I told you about that I use to live with till she went off to college?"

Alaric came up behind Jenna and wrapped his arms around her waist and kisses her neck gently. "Well she's not a girl anymore honey."

I blush again.

"Oh hush you." Jenna playfully swats at Alaric.

"It's nice to meet you Alaric." I say softly. I was genuinely happy that Jenna found someone that she seemed so in tune with.

"Eh call me Ric please." He smiles at me.

Damon clears his throat beside me. "Shall we go in?"

"Yes," Jenna says, "My stomach is growling I been dying for some good eggplant parmagiana. And hi Damon." Jenna smirks at Damon.

Damon mutters some unintelligible words receiving a playful glare from Jenna. We went inside and the hostess led us to our small round table in the back of the restaurant where it was more private. After some appetizers and explaining to Ric and Jenna on how Damon and I met, I ordered my third glass of wine and excuse myself to use the restroom.

Once I entered the restroom I lock the door behind me and sigh heavily. I was absolutely exhausted. Even though this shouldn't drain me emotionally it was. It shouldn't be I know that. I just always was this way. Always over analyzing everything.

"Elena let me in," Jenna knocks on the door interrupting my alone time. I unlock the door and Jenna rushes in locking the door behind her.

"You're lucky there isn't a line out there," Jenna smiles at me softly her cheeks tinted pink from a buzz I knew all too well that was coming. Living with Jenna for a few years taught me a thing or two about this woman. Nevertheless I love her.

I smile at Jenna and pretend to fix my hair, ignoring the fact that she is staring at me with raised eyebrows. I quirk and eyebrow up at her wondering why she is staring at me like this.

"So care to tell me what you are really doing with Damon?" Jenna suddenly said.

I was in shock to say the least. I thought Damon and I were doing pretty well, but apparently not. Not if Jenna could see right through us. And if she could see right through us, so won't everyone else.

"Don't get me wrong, whatever you and Damon are doing you are doing well, it's just I know Damon, Elena, and more importantly I _know _you." Jenna points out standing in front of me with her arms folded across her chest.

I honestly didn't know what to say so I settled for the simplest thing… the truth. I tell her everything starting from the beginning. I feel like I am on repeat. Everything I told her I told Caroline, except with Jenna I left out the moments we kissed.

"Interesting, well I am not going to say anything. I will be having a talk with Damon later. I won't let Ric know because then he would just go on a rampage and try to fix Damon up. So my advice to you is just be careful. I don't want to see you get hurt." With that she hugs me and leaves the restroom. I stood there dumbfounded for a few minutes. Getting ready to leave the bathroom I open the door only to have someone push me back in.

"Elena…" Damon smirks at me and drawls out my name in his usual annoying manner. He locks the door behind him and I raise an eyebrow at him. He wiggles his eyebrows back at me, his smirk still on his face.

"Damon what are you doing?" It amazes me how this one person can get under my skin and make me feel extreme annoyance one second and wanting sex the next.

He didn't answer but instead stalks over to me till my butt hits the counter. He places his hands on the counter on both sides of me, trapping me in like he did the other night. The only difference this time is that I am not scared. I look up at him and fold my arms over my chest.

"Whatever you are trying to do, it's not going to work. Besides we need to get back out there, I am sure our dinners will be out soon." I try move, but damn him for being stronger than me. Not knowing what else to do I did the only thing I could think of in the moment. For the first time I initiate something I thought I never would.

_I kiss him._

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**So what did you think? Please review **** and just a note... This is going to be the last chapter for a while that is in Elena POV. Next couple chapters on will be Damon POV. I can't resist doing this. What do you all think about that?**


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